Ask Jason LIVE!: Unpacking Startup Strategies with Real-Time Q&A | E1921

This Week in Startups is brought to you by…

Squarespace. Turn your idea into a new website! Go to https://www.Squarespace.com/twist for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain.

OpenPhone. Create business phone numbers for you and your team that work through an app on your smartphone or desktop. TWiST listeners can get an extra 20% off any plan for your first 6 months at http://www.openphone.com/twist

Eppo. Experimentation is how generation-defining companies win. Accelerate your experimentation velocity with Eppo. Visit http://www.geteppo.com/twist

*

Todays show:

Jason kicks off Ask Jason live! Six live guests ask questions on key topics, including prioritizing multiple founders (13:28), advice around moat for a startup (52:42), and whether not focusing on AI in a pitch will affect investment chances (1:02:38).

*

Timestamps:

(0:00) Jason kicks off another Ask Jason with 6 live guests!

(1:13) Sean asks about investment firms changing how they invest early on.

(11:42) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/twist

(13:28) Pierson of jellypod asks about prioritizing multiple founders for investments or accelerators

(22:54) OpenPhone - Get 20% off your first six months at http://www.openphone.com/twist

(24:47) Ann asks if they should raise venture capital to grow faster even though it means giving up some company ownership.

(32:01) Eppo. Accelerate your experimentation velocity with Eppo. Visit http://www.geteppo.com/twist

(39:56) Francis asks how to strike a balance between skepticism and enthusiasm when evaluating a company for investment, given that it's impossible to invest in every company.

(52:42) Hosum asks if explaining their startup's moat as current execution and future benefits after reaching product-market fit is enough to convince investors.

(1:02:38) Thom asks if not highlighting AI in our funding pitch will hurt our chances of getting investment.

*

Send us your questions for the next episode of Ask Jason LIVE! http://www.thisweekinstartups.com/askjason

*

Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

*

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

*

Thank you to our partners:

(11:42) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/twist

(22:54) OpenPhone - Get 20% off your first six months at http://www.openphone.com/twist

(32:01) Eppo. Accelerate your experimentation velocity with Eppo. Visit http://www.geteppo.com/twist

*

Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

*

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

*

Follow TWiST:

Substack: https://twistartups.substack.com

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

*

Subscribe to the Founder University Podcast: https://www.founder.university/podcast